Sterek Fic - Really Together (Part 2)
by brilliantstars
Summary: For lack of a better summary, Sourwolf has intimacy issues and Stiles wants him to get over them and finally pop his cherry. Rated M! R/R


Derek had told Stiles not to worry and that he would take care of everything after he left that night, all Stiles had to do was show up that Friday night. He kissed him on the forehead and Stiles made he promise again and again that he wasn't going to go back on his promise, and Derek just smiled against his skin and promised.

Stiles couldn't help but express his enthusiasm to Scott who tried his best to not how utterly grossed out he was at the thought of Derek and Stiles doing it.

"Well, are you nervous?" Scott asked, in attempt to try and be supportive.

"No, hell no!" Stiles waved his hand, "just horny and excited."

"Oh wow, too much information."

"Come on, dude! I've had to listen to yours and Allison's sex stories for months."

Scott sighed, "Just be careful then I guess."

"Be careful? That's the advice you're giving me on my quest to manhood?" Stiles said exasperated.

"It's a big deal. I mean I know I may sound lame, but I don't regret a thing with Allison. It was right and you're my best friend, and I just want you to know that's it's the right time with the right person."

"Dear god, you sound like an after school special." Stiles gave Scott a look, "but thanks I guess. And look I know you've never really got Derek and Me, but it is right. I want it to be him."

"Then I'm happy for you. You're really not nervous?"

Stiles shook his head and grinned.

"This conversation needs to end." Scott says, grinning back

When Stiles arrived at the Hale house later that night he had a weird feeling in the pit of his stomach. He couldn't tell if it was anticipation or pain from the supper he had scarfed down not too long ago.

Or maybe he was a little nervous. As badly as he wanted it, it was still his first time. God damn Scott for making sense.

"Just be cool, man." Stiles muttered to himself as he walked up Derek's front porch, "don't be a girl."

He knocked on the door a few times before entering the house.

"Derek?"

"Upstairs." He heard Derek reply from a distance

Stiles sauntered up the stairs and met Derek in the hallway.

"Heeeeeeeyyyy you." Stiles did a weird pointing thing with hands, _"what the fuck"_ he thought.

Derek tilted his head and smiled, "Hi."

Stiles kind of lingered in his spot, "Whats up!" he said with a nervous laugh

"Stiles, come here." Derek said, sensing the boys nervousness.

"Damn you and your werewolf senses." Stiles walked slowly over to him

"Well…" Derek began, putting his hands on Stiles' shoulders, "you reek of lust and anxiety."

Stiles rolled his eyes, "No fair." He pouted

Derek touched Stiles cheek gently, "you know, we don't have to do this." He said in a low voice.

"Oh hell no." Stiles retorted, "anxiety or not, we are doing this."

"You sound like someone who is planning a bank robbery. But if you're sure."

"Yes. Yes, Yes, Yes." Stiles replied

"Okay. So do you want to have something to eat first?"

"I already ate." Stiles said

"Me too."

They stared at each other intently before instinctively falling into one another and mashing their lips together. Stiles wrapped his arms around Derek's neck tightly, pulling him close.

"If you had said," Derek murmured between kisses, "you weren't sure, I would have died."

Stiles smiled into the kiss and nipped at Derek's bottom lip before pushing his tongue into the man's mouth. Derek's hands slinked down to Stiles' ass, then fell to the back of his thighs and he pulled the younger boy up into his arms; Stiles wrapped his legs around Derek's waist.

Stiles broke the kiss, "Wow, kinda taking my manhood away here a little."

"That's not all I'll be taking, trust me." Derek said gruffly as he walked them towards the bedroom, stopping to push Stiles against the wall for a moment and kissing him deeply.

They reached the bedroom and Derek set Stiles back down, "After you." Derek said.

Stiles scoffed and opened the door, "Dude." Was all he could say as he entered the room.

The air mattress had been replaced with an actual bed and the room smelled like vanilla, probably due to the numerous candles lit up around the room. The windows also now had curtains.

"Yeah manhood gone." Stiles said, but couldn't help but smile at the thought of Derek buying scented candles and drapes.

"Yeah, well. I figured it was time to get a bed. And, well I wanted it to be memorable for you. My first time wasn't and I guess this is kind of my do-over."

"You dreamed of vanilla scented candles during your first time?" Stiles grinned at Derek who looked a little embarrassed, "Thank you. I mean it, its…its perfect."

There was a beat.

"Wow, you got uh, a TV there too." Stiles gestured to the flat screen on the wall, "its…big." Stiles felt like an idiot for getting this nervous.

He felt a pair of arms around his waist and Derek's warm lips against his neckline. Stiles let his head fall back onto Derek's shoulder, letting out a breath.

"You're a closet romantic, aren't you?" Stiles breathed out

"Stiles?" Derek said against his lips before pressing his hand down on Stiles' cock through his jeans.

"Y-yeah."

"Shut up." Derek said darkly into Stiles' ear.

"Impossible." Stiles stammered

Derek unbuttoned Stiles jeans and dipped his hand inside, "How about now?" Derek said, licking Stiles' earlobe and wrapping his large hand around Stiles' cock.

"Ohhh, getting warmer." Stiles stuttered

Derek smirked and released his grip; Stiles whined. He pushed his jeans down and Stiles kicked them off, turning around to face the wolf.

"Hi." Stiles smiled, moving his hands under Derek's shirt and tracing his fingertips over his abdomen.

"Hi." Derek replied, hauling his shirt off and leaving Stiles with cornucopia of skin to put his lips on. Stiles latched them onto Derek's neck, nibbling a little at his pulse point. Derek moved his hand to Stiles neck to pull him in closer and pushed his plaid shirt off his shoulders. Of courses Stiles had about 3 layers on, but Derek quickly removed them all and pressed both their chests together; Stiles gasped.

Derek nuzzled his face down to Stiles chest, taking in his scent.

"You feel so good." Stiles breathed, "F-fuck." Derek took one of Stiles nipples into his mouth, flicking his tongue over the nub and rubbing the free one with his fingers.

Stiles laughs nervously and runs his hands up and down Derek's biceps in attempt to stop his trembling fingers, "I didn't think I'd be this nervous." He admits

"S'okay." Derek brushes against his lips, "I am too."

Stiles smooth's his thumb over Derek's cheekbone, "Y-you'll go slow, right? Just at first."

Derek nods.

"Okay." Stiles lets out a long breath, "I think I'm ready. Are you ready?"

"Yeah." Derek says shakily; they stare at each other briefly and Stiles wraps his arm around Derek's neck, leaning up to crush his lips against his. He kisses franticly across Derek's jawline and to his ear, where he whispers:

"I'm glad its you…not to get all sappy, but love you." he lets his head rest back against the pillow again.

"I love you too."

Stiles grins widely, "Okay," he says, "lets do this."

Derek half chuckles and moves his hand to line his cock up at Stiles' hole. He looks to Stiles one more time for the go ahead, and Stiles nods.

Derek slowly begins to push in.

And it hurts.

Like really fucking hurts.

Stiles can feel himself clamping down on Derek, every part of him wanting the intrusion to come to a halt because the feeling is too full, too painful and too much for Stiles to handle.

Stiles lets out a painful cry that he is sure he is going to regret later, but non the less, with each inch of Derek entering him the pain burns more and more and Stiles can't help but let out these strangled cries and whines. Shutting his eyes tight, he digs his fingertips into Derek's biceps hard. Once Derek is all the way in, Stiles' hands palm at his chest as a signal to stop and wait.

"Derek…h- it…h-urts" Stiles' groans

Derek looks down at Stiles face. He is wrecked with pain, his eyes are wet and he is shaking. Derek kisses his all over his face tenderly, before finding his lips.

"Do you want me to stop?" Derek mumbles into Stiles lips in an agonizing tone because the wolf in him wants to take over and fuck Stiles down into the mattress.

"N-no." Stiles stutters, "its okay. Move."

Stiles shaky hands move back to Derek's arms, and Derek rolls his hips slowly down into Stiles.

"Nghhh." Stiles bites down on his lip, a stray tear falling from his eye and down his cheek.

"Stiles…" Derek breathes

"Its okay." Stiles stutters again, "its okay. Y-your just, wow I f-feel like I have a…" Stiles couldn't find the words, "You're f-freakishly huge."

Derek shifts a little so he can lean down to kiss Stiles collarbone to offer comfort.

"Nnngh." Stiles whines

"Stiles" Derek says again sternly.

"N- fuck. Its okay, I just n-need to get used to…i-nside of me….Holy fuck, you're inside of me."

Derek rolls against Stiles hips even slower than before and Stiles buries his face into Derek's shoulder. Derek can feel the wetness from Stiles' eyes on his skin and a soft nip of Stiles' teeth on his skin. Derek kisses down his neck and across his shoulder. He runs his hand up and down Stiles trembling thigh in a soothing manner.

"Its okay." Derek whispers against Stiles, "Its okay. Relax. Just breathe."

Derek rocks against him and they continue at this slow pace for what feels like forever. Stiles keeps trembling and whining, clenching his legs to Derek's hips.

After a few more thrusts, Stiles had become silent. Just breathing heavily into Derek's shoulder. While he is still clung to Derek's body, he had stopped shaking. Derek takes this as a signal, and gradually pulls himself all the way out of Stiles and pushes back in with a bit more pressure.

Derek grunts and grasps at a handful of sheets below him and this time Stiles lets out a little groan against Derek's skin.

"Stiles…look at me."

Stiles let's his head fall back against the pillow. His eyes are red and glazed over and the expression on his face is blank, as if he doesn't know what he is feeling. His hands falls to Derek's waist and his eyes flutter with each slow thrust of Derek skin against his. He lets out a small, breathy moan and a smile slowly spreads across his face.

"O-ohh." Stiles finally moan's in relief, canting his hips up a little to meet Derek's thrusts, "O-h t-that's…good." He smiles a little bigger, closing his eyes and moaning again.

"Yeah?" Derek says against his cheek

"Yeah…fuck Derek."

They stumble upon each other's lips. The kiss is sloppy and uncoordinated, their tongues mashing together in a needy manner until they are moaning into each other's mouths.

"Faster. Go a little f-faster." Stiles breaths, "God yes."

Derek gripped Stiles thigh as a brace, he was quickening his thrusts at Stiles request and letting low growls escape from his throat. Stiles felt so good clenched around his cock, writhing underneath him and begging for more. Stiles gripped Derek's ass hard and pushing him in deeper and the wolf moaned loudly, obeying the boy's wishes.

"Yes, y-yes." Stiles moaned, "this—this is…sex is, s-so good." Stiles spread his legs wider, and moved his hand down to grip his cock, "Harder. Fuck me harder. Till I'm sore. Raw, god Derek, fuck me r-raw." Stiles babbled. Derek knew Stiles wouldn't be anymore silent during sex anyways, but his voice sounded wrecked.

Derek licked up Stiles neck and to his earlobe, licking around it, "Dirty." He murmured into Stiles ear. The bed had begun to creak as Derek smacked harder into Stiles' ass. "You want me to fuck you raw?"

Stiles grunted out a laugh and bucked his hips upward. Derek reached his arm around Stiles body between his back and the now dampened sheets and pulls them around so that Stiles is now on top of him.

"Uh, uhh. Um D-derek." Stiles felt oddly exposed this way, but Derek kept bucking his hips up into Stiles.

Derek ran his hand up flat against Stiles stomach and chest, to his neck and ran his fingers across his lips, "You look soo fucking good…ride me." Derek groaned.

Stiles slowly started to move up and down on Derek's hips.

"Shit." Stiles moaned, Derek had taken over the touching of Stiles cock keeping in time with Stiles movements, which had now become more erratic and fast. The new angle had given Stiles more control and as he rode Derek's hips he managed to find an angle that had Derek now hitting against his prostate.

"Oh my god", he groaned, "there, there, there" he moaned in an almost sing song voice, hands splayed against Derek's stomach.

"There?" Derek repeated, bucking his hips up and striking his prostate hard.

"Oh you fucking asshole.", Stiles moaned; eyes screwed shut, his mouth curved in a smile.

Derek sat himself up, desperate to feel Stiles lips. They mashed their lips together clumsily in all the passion, their lips now moved together not quite in a kiss but as if they were taking one breath together. Derek had his fingers buried into the mattress, stifling growls from his stomach. Stiles had his hands plastered to Derek's shoulders, using them as his anchors while he moved up and down on Derek's lap with uninhibited haste. The smacking of skin on skin became louder and quicker, Stiles eventually managed to moan,

"I-im close. Oh god in so close. Derek!" he bit down on Derek's shoulder. His stomach began to tighten and twist. He reached down and stroked his cock.

Derek flipped them around so he was on top again, pounding down into Stiles with whatever strength he had left. Stiles hooked his legs tightly around Derek's waste and dug his heels into his lower back to get him deeper.

Derek was breathing erratically, his eyes glued tight together. He pressed his forehead against Stiles but his head turned as if he was doing his best not to make eye contact.

"Hey," Stiles panted, taking Derek's face in his hands, "Hey look at me."

Derek opened his eyes to reveal that they were glowing red.

"Stiles..." he moaned painfully

"Its okay," Stiles breathed, kissing him again and again murmuring like Derek had done before, "It's okay". Derek grabbed for Stiles hands and pinned them above his head, enlacing their fingers together and squeezing them tightly. Stiles squeezed back, it was the only way he could let Derek know that he was perfect and that Derek was perfect and that this was everything he could want. He knew Derek's insecurities, about being violent and about Kate. He knew how nervous he was about being that way with Stiles.

"Derek," he squeezed back against Derek's hand, "Derek stay with me." Derek let out a harsh breath; he kissed against Stiles cheek in response.

"I'm gonna come.", Stiles moaned, stomach coiling, "Will you come with me?"

Derek grunted in response, hitting the headboard with his palm; digging his now elongated claws into the wood.

"Stiles, Stiles, S-"

"Mmm, Derek! Fuck." his hand gripping the back of Derek's neck, "Come for me, c-come inside me. Fuck!" Stiles arched his back and stroked his dick hard before he came in long ropes all over both their stomachs.

Derek thrust into him a few more times before letting out a purely animalistic moan and spilling into Stiles, dragging his claws down the headboard


End file.
